In the Hundred Acre Wood, Tigger searches for someone to bounce with him, but all of his friends are too busy getting ready for the upcoming winter. While he searches for a playmate, Tigger inadvertently destroys Eeyore’s house with a boulder. He later damages the complex pulley system that Rabbit has rigged up to remove the boulder, much to the latter’s frustration. The rest of Tigger’s friends say that they are not quite as bouncy as he is because they are not Tiggers like him. Tigger sadly wanders off in loneliness, wishing there was somebody else like him.
Wanting to play with Tigger, Roo asks if Tigger has a Tigger family he could bounce with. Tigger is fascinated by the idea, and the two go to visit Owl for advice on finding Tigger’s family. Owl shows them portraits of his own family and mentions the concept of family trees; Tigger accidentally knocks the portraits over. When he quickly hangs them back up, all of Owl’s ancestors appear to be perched on a single tree. Tigger inaccurately concludes that his family tree must be a real tree, and he and Roo go searching for it.
After searching the wood without turning up any giant, Tigger-striped trees, Tigger and Roo go back to Tigger’s house to search for clues to his family’s whereabouts. Tigger teaches Roo the awesome Whoop-de-Dooper-Loop-de-Looper-Alley-Ooper Bounce. They find a heart-shaped locket that Tigger hopes will contain a picture of his family, but it is empty. Roo suggests Tigger try writing a letter to his family, which Tigger does. Once he finishes, he puts it in the mailbox and lets the wind carry it away, hoping it will take it to his family.
When Tigger’s letter gets no response, Roo gathers Tigger’s friends together to write him a letter; everyone contributes a bit of friendly advice and signs it “your family”. Tigger is overjoyed to receive the letter, however, while “reading between the lines”, he misinterprets it and announces that his whole family is coming to visit him tomorrow. Tigger’s friends do not have the heart to tell Tigger that the letter is from them, so they disguise themselves as Tiggers and attend his family reunion. Rabbit does not join in, but, rather, berates them for not getting ready for the approaching winter and storms off.
Tigger completely falls for the Tigger disguises until Roo attempts Tigger’s complex Whoop-de-Dooper-Loop-de-Looper-Alley-Ooper Bounce, crashes into the closet again, and knocks his mask off. Tigger is struck with astonishment and soon finds out that all of his friends are in on it. Frustrated and thinking that his friends have betrayed him, Tigger angrily goes out in a ferocious snowstorm to search for his family.
Tigger’s friends all feel very guilty, humiliated, and worried, including Roo, who becomes heartbroken. He later comes over to Pooh’s house, crying and tearfully claiming that it was his fault Tigger had left, for he wanted Tigger as a big brother, and they form an expedition to find him and convince Rabbit to lead them. They find Tigger sitting in a large tree with patches of snow on the trunk that resemble stripes, which Tigger has mistaken for his family tree. Rabbit insists Tigger come home, but Tigger refuses to leave his “family tree” until his (nonexistent) Tigger family returns; upon arguing, Tigger’s shouting causes an avalanche. Tigger bounces his friends to safety in the tree branches, but is swept away by the snow himself. Roo performs a perfect Whoop-de-Dooper-Loop-de-Looper-Alley-Ooper Bounce and rescues Tigger. The two then perform the bounce together to escape the avalanche and land back on the tree.
When the avalanche subsides, Tigger realizes that he has lost the letter from his family. All his friends each recite their parts of the letter from memory, and Tigger finally sees that they are his real family. He throws a new family reunion party with presents for everyone. Eeyore gets a new house, Pooh gets a lifetime supply of honey, Piglet gets a year’s worth of firewood, Tigger promises Rabbit that he will look where he is bouncing and Roo receives the heart-shaped locket. Christopher Robin then takes a picture of Roo, Tigger, and the rest of their family to go in it. The film ends with the camera backing away from the family photo as the locket closes up.